Charles White Whittlesey was born January 20, 1884 in Florence, Wisconsin. He was the eldest son of Frank R. and Annie Whittlesey and had three younger brothers: Russell (b. July 1887), Elisha (b. February 1892) and Melzar (b. July 1893). All of the children were born in Wisconsin but, sometime between 1893 and 1900, the family relocated to Pittsfield, Massachusetts where Frank was employed by General Electric Co., first as a Purchasing Agent and later as a Production Manager.
Whittlesey attended Pittsfield High School and after graduation entered Williams College. While at Williams, he was a member of the Delta Psi fraternity and the Gargoyle Society. He was Editor- in-Chief of the Gulielmensian (the College yearbook), and Editor of both the Williams Literary Monthly and the Williams Record. He contributed to these publications frequently and, perhaps as a result of this prolificacy, was asked to write the essay on the "Literary Enterprises" of the Class of 1905 for the Class Book. His classmates, who nicknamed him both "Count" and "Chick", voted Whittlesey the third brightest man in the Class of 1905.
After his graduation from Williams, Whittlesey attended Harvard Law School, from which he graduated in 1908. He then went into law practice in New York City with the firm of Murray, Prentice & Howland from 1908 to 1911. In 1911, he entered practice with his friend and classmate, J. Bayard Pruyn, at 2 Rector Street, New York City. He remained with Pruyn & Whittlesey until August 8, 1917, when he was placed on active duty and asked to report to Camp Upton in Yaphank, Long Island. Here he received three months of training prior to his term of service in Europe. One year prior to this, in August 1916, Whittlesey had graduated from the military training camp at Plattsburgh, New York.
In Europe, Whittlesey served with the 77th Division, 308th Battalion, Headquarters Company. He was involved in defensive endeavors, first behind the British front and later in the Luneville Defensive Sector. Beginning in August 1918, Whittlesey's Division entered real combat in the Vesle, Aisne, Argonne and Meuse offensives. Whittlesey gained world-wide recognition in October 1918 when the companies of his battalion, which were part of a campaign against the Germans in the Argonne Forest, were cut off for several days without adequate supplies of food or ammunition. Though it was often blamed on Whittlesey's own over-zealousness and inexperience, the troops of the 308th were left vulnerable to being surrounded by the enemy. Their own successful advance, and the inability of the Allied troops on the flanks to advance, had left them in such a position.
On October 2nd, when the companies of the 308th Battalion were first surrounded, they numbered 463 men. By October 7th, when Whittlesey's troops were rescued, they had been reduced to 194, alive and unwounded. While the 308th Infantry was cut off in the 'Pocket', a hill between Charleveaux Brook and the old Roman road and railroad in that sector, they were subjected constantly to machine gun and trench mortar attacks by well-supplied German troops. In addition, the 308th endured bombing raids by their own troops, the 50th Aero Squadron, who were confused as to the coordinates of the 'Pocket'. The runner chain from the 'Pocket' to Headquarters had been broken and the only means of communication was by use of homing pigeons. The last pigeon, Cher Ami, was used on October 4th to stop this friendly barrage.
Early on October 7th, the day that relieving Allied troops arrived, the German Commanding Officer who surrounded the 308th sent a letter to Whittlesey by an American prisoner requesting his battalion's surrender. Whittlesey and George McMurtry, his second- in-command, refused to acknowledge this request and even pulled in the white panels used to signal Allied planes for fear the Germans would mistake them for surrender flags. It was widely reported in the American press that Whittlesey had responded "Go to Hell!" immediately upon reading the letter. He later denied having made the statement, suggesting that no reply was necessary.
The eventual relief of the 308th Infantry occurred when several runners were able to break through the German lines to the south and lead the advancing troops to the 'Pocket'. Whittlesey was promoted from Major to Lieutenant Colonel upon the relief of his beleaguered troops. He was relieved from further duty on October 29th and returned to the United States. On December 5th, through the issue of Special Orders No. 259 from Headquarters at Fort Dix, NJ, he was honorably discharged from the United States Army. The following day, December 6th, he was named a recipient of the Congressional Medal of Honor, the highest award given by the U.S. Army.
After his discharge, Whittlesey returned to his law practice. He remained at Pruyn & Whittlesey from 1919 to 1920, when he became an associate at White & Case. As a national hero, he was frequently called upon to speak about his experiences in the War. A modest and sensitive man, Whittlesey was uncomfortable with the attention he was given and revealed as little detail as possible regarding events in the 'Pocket'. His public speaking was limited almost entirely to praising the enlisted men with whom he had served, the common soldiers who received no recognition for their uncommon bravery and patriotism.
Whittlesey chaired the Red Cross Roll Call in New York City beginning in late 1919, perhaps out of a sense of duty to aid those men with whom he had served and who were suffering after their return to the States. In 1921, he was promoted to Colonel and given command of the 308th Infantry Regiment in The Organized Reserves, a post he did not feel he could refuse. He also was asked to act as a pall bearer at the ceremonies to honor the Unknown Soldier at Arlington National Cemetery, yet another reminder of all the pain caused by the War.
On November 24, 1921, Whittlesey booked passage on the S.S. Toloa, a steamship owned by the United Fruit Co. bound for Havana. Prior to this, he had put his affairs in order and paid the rent to his landlady for the following month. On November 26th, after having stayed up late drinking and talking with other passengers, Whittlesey walked to the rail of the ship and jumped overboard. None of his friends or relatives had known about his travel plans and were thus disbelieving when the news arrived from the captain of the ship that Whittlesey had been lost at sea and that he had left behind letters to those close to him. The letters were addressed to his parents, his brother Elisha, his brother Melzar, his uncle Granville Whittlesey, and to his friends George McMurtry, J. Bayard Pruyn, Robert Forsyth Little and Herman Livingston, Jr. None of the letters revealed the reason for his suicide and the recipients refused to make them public.
Several theories existed at the time as to what had pushed Whittlesey to such depths of depression. Those close to him believed that his death could be counted among the War casualties in as much as it was his sensitivity to the constant reminders of the destruction of the War that drove him to suicide. Some believed that his suicide was caused by feelings of guilt: the possibility that he had given incorrect coordinates to the 'Pocket', thereby causing friendly fire, or having refused to surrender to the Germans, leading to increased loss among his men. Others believed that it was his modesty and inability to adjust to the life of a hero that caused the depression that eventually ended his life. Whatever the exact reason may have been, it is clear that Whittlesey's death was indirectly related to the unhappiness which befell him after his experiences in the War.
Whittlesey asked Pruyn to serve as executor of his will in the letter which he wrote from the S.S. Toloa. This will, which was found among Whittlesey's papers in his law office, left the original copy of the German surrender request to George McMurtry. To his closest friend, Pruyn, Whittlesey left his Cross of the Legion of Honor. Whittlesey cleared his brother, Melzar, from any debt that he owed and left the remainder of his belongings to his mother.
Years after his death, accounts of the 'Lost Battalion' continued to be written and Whittlesey continued to be praised. In 1948, the Charles White Whittlesey Room was dedicated at the Williams Club in New York City. At the ceremonies, which were attended by George McMurtry and Williams College President James P. Baxter, a portrait of Colonel Whittlesey was unveiled. His friends and comrades did not forget him.